Real Estate Investment Properties for Sale in Oakland, MD

Looking for investment property in Oakland, MD with high ROI ?

Explore a variety of short-term homes & houses in Oakland, MD. Invest wisely with VRBO & Oakland, MD Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Oakland, MD

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
609 Southern Pines Drive Oakland, MD Welcome to your next dream home! Nestled on a 4-acre wooded lot, this custom built residen...	4 beds \| 3 baths \| 2,250 sq.ft.	$425,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 6.13% Airbnb Rental Income: $1631 Traditional Rental Income: $3296 Airbnb ROI: 0.79% Traditional ROI: 6.13%
24 TRAILSIDE WAY Oakland, MD Tucked in the Silver Ridge community at Deep Creek Lake, this inviting home blends rustic ...	4 beds \| 4 baths \| N/A	$555,000	Airbnb cash on cash: 0.16% Traditional cash on cash: 5.16% Airbnb Rental Income: $1631 Traditional Rental Income: $3765 Airbnb ROI: 0.16% Traditional ROI: 5.16%
98 BEAR RUN Road Oakland, MD Make it your own! This 2-acre parcel comes with two additional parcels of 17.96 and 24.23 ...	3 beds \| 2 baths \| 1,080 sq.ft.	$550,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 3.29% Airbnb Rental Income: $1148 Traditional Rental Income: $2510 Airbnb ROI: -0.1% Traditional ROI: 3.29%
25 SILVER TREE Lane Oakland, MD Beautiful lake access retreat located in the Silver Tree Landings community with an availa...	5 beds \| 4 baths \| 2,364 sq.ft.	$749,900	Airbnb cash on cash: -0.2% Traditional cash on cash: 1.81% Airbnb Rental Income: $1968 Traditional Rental Income: $2858 Airbnb ROI: -0.2% Traditional ROI: 1.81%
1544 STOCKSLAGER Road Oakland, MD Enjoy lakefront living at its finest in this beautifully remodeled home with a private doc...	5 beds \| 4 baths \| 3,456 sq.ft.	$1,750,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 1.2% Airbnb Rental Income: $1968 Traditional Rental Income: $4663 Airbnb ROI: -0.78% Traditional ROI: 1.2%
3749 MARYLAND Highway Oakland, MD Set on a beautiful lot in Deep Creek, Maryland, this stunning property offers the perfect ...	2 beds \| 2 baths \| 2,015 sq.ft.	$325,000	Airbnb cash on cash: 0.42% Traditional cash on cash: 5.59% Airbnb Rental Income: $1132 Traditional Rental Income: $2334 Airbnb ROI: 0.42% Traditional ROI: 5.59%
267 SAN FRANCISCO Street Oakland, MD Welcome to your secluded Deep Creek retreat! This stunning property offers expansive lake ...	4 beds \| 3 baths \| 3,278 sq.ft.	$899,900	Airbnb cash on cash: -0.53% Traditional cash on cash: 1.5% Airbnb Rental Income: $1631 Traditional Rental Income: $2874 Airbnb ROI: -0.53% Traditional ROI: 1.5%
467 PARADISE RIDGE Road Oakland, MD Panoramic mountain and lake views set the tone at this lake access home in Paradise Ridge,...	4 beds \| 4 baths \| 3,780 sq.ft.	$799,900	Airbnb cash on cash: -0.68% Traditional cash on cash: 2.7% Airbnb Rental Income: $1631 Traditional Rental Income: $3685 Airbnb ROI: -0.68% Traditional ROI: 2.7%
126 LEO FRIEND Road Oakland, MD Perched above the treetops with panoramic lake views, this three-level retreat blends comf...	4 beds \| 3 baths \| 2,235 sq.ft.	$529,900	Airbnb cash on cash: 0.6% Traditional cash on cash: 4.69% Airbnb Rental Income: $1631 Traditional Rental Income: $3200 Airbnb ROI: 0.6% Traditional ROI: 4.69%
285 LAKE SHORE Drive Oakland, MD Nestled on 1.52 private acres with 500 feet of frontage on Deep Creek Lake, this 5-bedroom...	5 beds \| 5 baths \| 2,593 sq.ft.	$1,149,800	Airbnb cash on cash: -0.26% Traditional cash on cash: 2.94% Airbnb Rental Income: $1968 Traditional Rental Income: $4868 Airbnb ROI: -0.26% Traditional ROI: 2.94%
449 S 3RD Street Oakland, MD Welcome to this beautifully updated 1901 home in the heart of downtown Oakland, where hist...	4 beds \| 2 baths \| 1,928 sq.ft.	$275,900	Airbnb cash on cash: 1.76% Traditional cash on cash: 7.55% Airbnb Rental Income: $1631 Traditional Rental Income: $2676 Airbnb ROI: 1.76% Traditional ROI: 7.55%
565 GLENDALE Road unit: 106 B #106 B Oakland, MD Ground-floor end unit with lake views at Silver Tree Suites. This one-bedroom layout packs...	1 beds \| 1 baths \| N/A	$229,900	Airbnb cash on cash: 1.02% Traditional cash on cash: 6.1% Airbnb Rental Income: $1077 Traditional Rental Income: $1813 Airbnb ROI: 1.02% Traditional ROI: 6.1%
328 STOOL ROCK Road Oakland, MD Designed and built for the sellers, this 4 bedroom, 2.5 bath home is a true showcase of cr...	4 beds \| 3 baths \| 1,860 sq.ft.	$545,000	Airbnb cash on cash: 0.45% Traditional cash on cash: 4.15% Airbnb Rental Income: $1631 Traditional Rental Income: $3055 Airbnb ROI: 0.45% Traditional ROI: 4.15%
565 GLENDALE Road unit: 212A #212A Oakland, MD Silver Tree Suites offers 350' of pristine shoreline at Deep Creek Lake with western expos...	1 beds \| 1 baths \| 527 sq.ft.	$199,000	Airbnb cash on cash: 1.52% Traditional cash on cash: 7.75% Airbnb Rental Income: $1077 Traditional Rental Income: $1886 Airbnb ROI: 1.52% Traditional ROI: 7.75%
1001 SUTTER Lane Oakland, MD Discover the ultimate mountain-lake getaway in this stunning 5BR Southern-style home on a ...	5 beds \| 6 baths \| 6,550 sq.ft.	$799,000	Airbnb cash on cash: -0.16% Traditional cash on cash: 6.23% Airbnb Rental Income: $1968 Traditional Rental Income: $6210 Airbnb ROI: -0.16% Traditional ROI: 6.23%
2725 STOCKSLAGER Road Oakland, MD Welcome to 2725 Stockslager Road, one of Deep Creek Lake's most coveted properties. This c...	5 beds \| 7 baths \| 5,376 sq.ft.	$2,350,000	Airbnb cash on cash: -1.38% Traditional cash on cash: 0.76% Airbnb Rental Income: $1968 Traditional Rental Income: $6125 Airbnb ROI: -1.38% Traditional ROI: 0.76%
723 KINGS Oakland, MD ""Charming two-story home situated on a beautiful .292-acre level lot in a prime location ...	4 beds \| 3 baths \| N/A	$359,700	Airbnb cash on cash: 1.42% Traditional cash on cash: 6.8% Airbnb Rental Income: $1631 Traditional Rental Income: $2986 Airbnb ROI: 1.42% Traditional ROI: 6.8%
163 MITCHELL Drive Oakland, MD Nestled in the charming Mitchell Manor community, this delightful split-level home offers ...	3 beds \| 3 baths \| 2,242 sq.ft.	$314,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 9.12% Airbnb Rental Income: $1148 Traditional Rental Income: $3270 Airbnb ROI: 0.65% Traditional ROI: 9.12%
1737 KING WILDESEN Road Oakland, MD Nestled on 10 secluded acres of serene woodland and open fields, this traditional cedar-si...	3 beds \| 2 baths \| 1,736 sq.ft.	$285,500	Airbnb cash on cash: 0.82% Traditional cash on cash: 8.94% Airbnb Rental Income: $1148 Traditional Rental Income: $2950 Airbnb ROI: 0.82% Traditional ROI: 8.94%
315 COOLIDGE Avenue Oakland, MD Well maintained brick rancher located in the heart of Oakland. This home offers a large ki...	3 beds \| 2 baths \| 1,600 sq.ft.	$269,500	Airbnb cash on cash: 0.91% Traditional cash on cash: 7.51% Airbnb Rental Income: $1148 Traditional Rental Income: $2447 Airbnb ROI: 0.91% Traditional ROI: 7.51%
531 GLENDALE Road unit: B302 #B302 Oakland, MD Experience effortless lakeside living at its finest in this spacious 2-bedroom, 1-bath uni...	2 beds \| 1 baths \| 887 sq.ft.	$369,000	Airbnb cash on cash: 0.13% Traditional cash on cash: 3.68% Airbnb Rental Income: $1132 Traditional Rental Income: $1981 Airbnb ROI: 0.13% Traditional ROI: 3.68%
333 SLOAN TRACT Road Oakland, MD Charming cabin off the coveted Lake Shore Drive offering seasonal lake views. This home ha...	4 beds \| 4 baths \| 1,492 sq.ft.	$475,000	Airbnb cash on cash: 0.56% Traditional cash on cash: 4.08% Airbnb Rental Income: $1631 Traditional Rental Income: $2737 Airbnb ROI: 0.56% Traditional ROI: 4.08%
1875 PYSELL CROSSCUT Road Oakland, MD With a new price you don't want to miss this chance! Beautifully maintained 5 bedroom 5 ba...	5 beds \| 5 baths \| 3,664 sq.ft.	$749,000	Airbnb cash on cash: 0.35% Traditional cash on cash: 5.49% Airbnb Rental Income: $1968 Traditional Rental Income: $5042 Airbnb ROI: 0.35% Traditional ROI: 5.49%
20160 GARRETT Highway unit: G507 Oakland, MD Experience lakefront living with this charming two-level condo at Will O the Wisp at Deep ...	2 beds \| 1 baths \| 912 sq.ft.	$389,000	Airbnb cash on cash: 0.16% Traditional cash on cash: 3.06% Airbnb Rental Income: $1132 Traditional Rental Income: $1811 Airbnb ROI: 0.16% Traditional ROI: 3.06%
565 GLENDALE Road unit: 210A #210A Oakland, MD Studio unit at Silver Tree Suites, one of Deep Creek Lake's most premier condo/hotel commu...	1 beds \| 1 baths \| 382 sq.ft.	$160,000	Airbnb cash on cash: 2.25% Traditional cash on cash: 10.01% Airbnb Rental Income: $1077 Traditional Rental Income: $1895 Airbnb ROI: 2.25% Traditional ROI: 10.01%
697 MONTE VISTA Road Oakland, MD Tucked away just minutes from downtown Oakland, MD, lies a home that truly surprises with ...	5 beds \| 4 baths \| 3,682 sq.ft.	$339,000	Airbnb cash on cash: 2.44% Traditional cash on cash: 11.48% Airbnb Rental Income: $1968 Traditional Rental Income: $4331 Airbnb ROI: 2.44% Traditional ROI: 11.48%
1909 PYSELL CROSSCUT Road Oakland, MD Welcome to a private retreat on 4 acres with sweeping views and a large front yard, just m...	4 beds \| 5 baths \| 2,970 sq.ft.	$865,000	Airbnb cash on cash: -0.16% Traditional cash on cash: 4.39% Airbnb Rental Income: $1631 Traditional Rental Income: $4836 Airbnb ROI: -0.16% Traditional ROI: 4.39%
961 CEDAR Lane Oakland, MD Tucked away in the woods on 1.72 acres, this stunning 4-bedroom, 2.5-bath mountain retreat...	4 beds \| 3 baths \| 1,920 sq.ft.	$359,000	Airbnb cash on cash: 1.53% Traditional cash on cash: 6.93% Airbnb Rental Income: $1631 Traditional Rental Income: $2991 Airbnb ROI: 1.53% Traditional ROI: 6.93%
3930 MAYHEW INN Road Oakland, MD 2 for 1 on 2 .3 +/- acres! Remodeled 2BR 2BA cottage with auxiliary building that has an o...	3 beds \| 3 baths \| 2,227 sq.ft.	$399,900	Airbnb cash on cash: -0.14% Traditional cash on cash: 5.73% Airbnb Rental Income: $1148 Traditional Rental Income: $2967 Airbnb ROI: -0.14% Traditional ROI: 5.73%
52 DAM VIEW Drive Oakland, MD Panoramic Lake views in the Bray Run community, just minutes from Deep Creek Lake, state p...	4 beds \| 6 baths \| 3,032 sq.ft.	$1,087,900	Airbnb cash on cash: -0.56% Traditional cash on cash: 3.91% Airbnb Rental Income: $1631 Traditional Rental Income: $5698 Airbnb ROI: -0.56% Traditional ROI: 3.91%
104 PINE TOP Trail Oakland, MD Here's your chance to purchase a cute Chalet with just about 7 acres. .This home and acrea...	3 beds \| 4 baths \| 1,596 sq.ft.	$425,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 6.41% Airbnb Rental Income: $1148 Traditional Rental Income: $3334 Airbnb ROI: -0.04% Traditional ROI: 6.41%
5024 CRANESVILLE Road Oakland, MD Just Reduced!! Charming 3-Bedroom Home with Scenic Mountain & Valley Views. Nestled on a 1...	3 beds \| 3 baths \| 2,128 sq.ft.	$399,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 6.14% Airbnb Rental Income: $1148 Traditional Rental Income: $3081 Airbnb ROI: -0.04% Traditional ROI: 6.14%
63 WALLMAN Road Oakland, MD Remodeled Rancher Near the North Branch Potomac River This charming 3-bedroom, 1-bath ranc...	3 beds \| 1 baths \| 816 sq.ft.	$174,900	Airbnb cash on cash: 2.79% Traditional cash on cash: 9.85% Airbnb Rental Income: $1148 Traditional Rental Income: $1944 Airbnb ROI: 2.79% Traditional ROI: 9.85%

Real Estate investment in Oakland, MD

There are 74 properties for sale in the city of Oakland . The median list price in Oakland is $372,000 and the average price per square foot is $193. In April 2026, the average monthly cash on cash return in Oakland is 2.00%. The average monthly rental income in Oakland is $2,547.

Oakland, MD Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 74 investment properties available for sale in Oakland.

In 2026, the best neighborhood to buy investment property is Oakland.

The ROI for Long-Term is higher than the Short-Term in Oakland with average rental income of $2,547.

Your search for investment property begins and ends here

Investment Property for Sale in Oakland, MD

609 Southern Pines Drive

Oakland, MD

4 beds | 3 baths | 2,250 sq.ft.

$425,000

Airbnb cash on cash: 0.79%

Traditional cash on cash: 6.13%

Airbnb Rental Income: $1631

Traditional Rental Income: $3296

Airbnb ROI: 0.79%

Traditional ROI: 6.13%

24 TRAILSIDE WAY

Oakland, MD

4 beds | 4 baths | N/A

$555,000

Airbnb cash on cash: 0.16%

Traditional cash on cash: 5.16%

Airbnb Rental Income: $1631

Traditional Rental Income: $3765

Airbnb ROI: 0.16%

Traditional ROI: 5.16%

98 BEAR RUN Road

Oakland, MD

3 beds | 2 baths | 1,080 sq.ft.

$550,000

Airbnb cash on cash: -0.1%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $1148

Traditional Rental Income: $2510

Airbnb ROI: -0.1%

Traditional ROI: 3.29%

25 SILVER TREE Lane

Oakland, MD

5 beds | 4 baths | 2,364 sq.ft.

$749,900

Airbnb cash on cash: -0.2%

Traditional cash on cash: 1.81%

Airbnb Rental Income: $1968

Traditional Rental Income: $2858

Airbnb ROI: -0.2%

Traditional ROI: 1.81%

1544 STOCKSLAGER Road

Oakland, MD

5 beds | 4 baths | 3,456 sq.ft.

$1,750,000

Airbnb cash on cash: -0.78%

Traditional cash on cash: 1.2%

Airbnb Rental Income: $1968

Traditional Rental Income: $4663

Airbnb ROI: -0.78%

Traditional ROI: 1.2%

3749 MARYLAND Highway

Oakland, MD

2 beds | 2 baths | 2,015 sq.ft.

$325,000

Airbnb cash on cash: 0.42%

Traditional cash on cash: 5.59%

Airbnb Rental Income: $1132

Traditional Rental Income: $2334

Airbnb ROI: 0.42%

Traditional ROI: 5.59%

267 SAN FRANCISCO Street

Oakland, MD

4 beds | 3 baths | 3,278 sq.ft.

$899,900

Airbnb cash on cash: -0.53%

Traditional cash on cash: 1.5%

Airbnb Rental Income: $1631

Traditional Rental Income: $2874

Airbnb ROI: -0.53%

Traditional ROI: 1.5%

467 PARADISE RIDGE Road

Oakland, MD

4 beds | 4 baths | 3,780 sq.ft.

$799,900

Airbnb cash on cash: -0.68%

Traditional cash on cash: 2.7%

Airbnb Rental Income: $1631

Traditional Rental Income: $3685

Airbnb ROI: -0.68%